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Call for ContributionsHETEROCYCLES Special Issue Vol. 99 in honor of Professor Tohru Fukuyama on 70th Birthday

Submission deadline: September 10, 2018
On the occasion of Professor Tohru Fukuyama's 70th birthday, HETEROCYCLES editorial office is planning to publish special anniversary issue on April 1, 2019 as Vol. 99. Authors are invited to submit their work to this topical issue.
Authors wishing to submit their manuscript should contact editorial office via e-mail by the end of May, 2018. Manuscript should reach the editorial office no later than September 10, 2018.
Contact: submit@heterocycles.com

March 5, 2018

Heterocycles Award
HETEROCYCLES is pleased to announce Heterocycles Award.
In recognition of an outstanding oral presentation at the 47th Congress of Heterocyclic ChemistrySee more

December 13, 2017

Call for ContributionsHETEROCYCLES Special Issue Vol. 97 in honor of Professor Kiyoshi Tomioka on 70th Birthday

Submission deadline: February 15, 2018
On the occasion of Professor Kiyoshi Tomioka's 70th birthday, HETEROCYCLES editorial office is planning to publish special anniversary issue on September 1, 2018 as Vol. 97. Authors are invited to submit their work to this topical issue.
Authors wishing to submit their manuscript should contact editorial office via e-mail by the end of November, 2017. Manuscript should reach the editorial office no later than February 15, 2018.
Contact: submit@heterocycles.com

■ Sphingolipids and Glycosphingolipids — Their Synthesis and Bioactivities

Abstract

Chemistry of sphingolipids and glycosphingolipids is discussed with main emphasis on their synthetic methods. Microbial, plant, animal and marine sphingolipids and glycosphingolipids with the following biological roles are treated in this review: (i) inducers of fruiting body formation in Basidiomycetes, (ii) water barrier and supporting material of animal epidermis, and (iii) bioregulators of medicinal interests including immunostimulants.

■ Synthesis of Various Substituted Spiro- and Bicyclethiazolidine-2-thiones by a Multicomponent Reaction and Biological Evaluation in vitro

Abstract

A series of novel spiro[4.4] and bicycle[3.3.0]-N-substituted thiazolidine-2-thiones were obtained by a multicomponent reaction under mild conditions. Each of the synthesized compounds was evaluated for their cytotoxic activity and antibacterial activity. Some of them exhibited significantly inhibited proliferation of human tumor cell lines and moderate inhibitory effect on fungi.

Abstract

The reactions of pyridinium 2-alkylthio-1-benzoyl-2-thioxoethylides with dimethyl acetylenedicarboxyate in THF at the reflux temperature afforded the unexpected products, dimethyl 2-alkylthio-4a-phenyl-4aH,5aH-thiino[3’,4’:4,5]oxazolo[1,3-b][1,3]oxazepine-3,4-dicarboxylates, together withdimethyl 10aH-4-alkylthio-5-benzoylpyrido[1,2-d][1,4]thiazepine-1,2- dicarboxylates.

Abstract

A novel bis-arylated indole derivative, 2,5-bis(2-naphthyl)-1-methyl-1H-indole, was prepared and characterized. This compound shows the highly pure blue emissions both in solution and solid state which were ascribed to the expanded π-conjugation by introduction of two 2-naphthyl groups at the 2 and 5 positions on the indole ring. From X-ray crystallographic results this molecule exhibited the intermolecular CH–π interactions which consisted two dimensional (2D) herringbone structure.

Abstract

New 5-(9H-Fluoren-9-ylidene)- and 5-(1H-indan-1-ylidene)-2-thioxo-4-thiazolidinones 3a,b were synthesized Eco-friendly under microwave irradiation (MWI). These compounds undergo alkaline hydrolysis to afford the corresponding thiol derivatives 4a,b, which cyclized into polysubstituted thiazoles 6a-h using arylazomalononitriles 5a-d as nucleophilic agents. Some selected products were tested for their antimicrobial activities. The equilibrium geometries of the studied compounds were calculated at the B3LYP/6-31G(d) level of the density functional theory (DFT). Conformational analysis has been carried out to determine the most stable conformers. The relative stability of the azo and hydrazo tautomers has been investigated. The HOMO-LUMO energy gap is used in rationalizing the reactivity of the studied compounds.

*Laboratory of Applied Chemistry, University of May 8th, 1945, BP 401, Guelma, Algeria

Abstract

The synthesis of a new series of N-substituted perhydro-1,3-oxazin-2-ones containing N-phenylsulfonamide is described. The compounds 7a–7f were obtained in a one-pot reaction from chlorosulfonyl isocyanate, selected 1,3- halogenoalcohols and various aromatic amines in alkaline conditions, to give the target N-heterocyclic 6-membered ring compounds with good yields. The X-ray crystal structure of N-[(N-4-fluorophenyl)sulfamoyl]perhydro-1,3-oxazin-2-one 7d was solved. All the synthesized compounds have been screened for their in-vitro antibacterial activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Structures of 7d and 6e can be further optimized to give new potent antibacterial agents with structures significantly different from those of existing classes of antibiotics.

■ Synthesis and Mesomorphic Properties of a Series of Phenyl 6-(4-Alkoxyphenyl)nicotinates

Abstract

A new homologous series of phenyl 6-(4-alkoxyphenyl)nicotinates (nOPNicP, n = 3-7) was synthesized. The entire synthetic procedure was completed in a short two-step process. Very good two-step overall yields of 70-80% were obtained and high α–regioselective addition of Grignard reagents to 1-acylnicotinium salts was observed while preparing this series of liquid crystals. Spectral analyses were in accordance with the expected structures. Their thermotropic behaviours were studied using polarizing optical microscopy and further confirmed by differential scanning calorimetry. Smectic A phase was found to be the only mesophase in this series of compounds.

*Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Ibaraki 305, Japan

Abstract

Three new C15 polyacetylenes 1, 2, and 3, together with two known C15 polyacetylenes 4 and 5 were isolated from the seedlings of sunflower Helianthus annuus L. cv Russia, and their structures were elucidated by spectroscopic data and chemical means. Compounds 1, 2, 4, and 5 exhibited antimicrobial activity against Staphyrococcus aureus and especially compound 1 showed strong activity.

Abstract

A series of N´-(2-benzylthio-4-chlorobenzenesulfonyl)-1H- pyrazole-1-amidines (23-36) were synthesized by the reaction of 3-amino-2-(benzenesulfonyl)guanidines (18-22) with adequate 1,3-diketones. The compounds 23, 24, 26, 30, 31, 34 and 35 were tested in vitro in the full NCI 60 cell panel. The most potent compound in the series (26) showed substantial activity toward some cell lines of leukemia and cancer cells of lung, colon, CNS, melanoma, renal, prostate and breast (GI50 in the range 2.30-9.47 μM).

■ Simple Synthesis of Pratosine and Hippadine by Intramolecular Palladium-Catalyzed Cyclization and Decarboxylation

Abstract

The palladium-catalyzed cyclization of dimethyl 1-(2-bromo-4,5-dimethoxybenzyl)indole-2,3-dicarboxylate in the presence of tetrakis(triphenylphosphine)palladium(0) and potassium acetate in hot 1,4-dioxane produced the 7H-pyrrolo[3,2,1-de]phenanthridine derivative, which was converted to pratosine by hydrolysis and decarboxylation. In a similar manner, hippadine was also prepared.

■ Microwave-Assisted Synthesis of 3,5-Disubstituted Thiohydantoins Using Functional Ionic Liquid as Soluble Support

Abstract

A new approach for the syntheses of 3,5-disubstituted thiohydantoins was described using functionalized ionic liquid as soluble support. The products were obtained in good yields and purities after cyclization-cleavage from the ionic-liquid-supported under microwave irradiation, the ionic-liquid-supported species can there be purified from the reaction mixture by simple washing, and no chromatographic purification were needed during the synthesis.

Abstract

Nine andrographolide derivatives (A2, A3a-b, A4a-e, A5) were synthesized to study the antifeedant activities of these derivatives and tutin against Mythimna separata. Compared with tutin, the nine derivatives exhibited better antifeedant activities, and six of them showed different mortality effects. It was concluded that the potent insecticidal agents are A2 (14-deoxy-11,12-didehydro-andrographolide), A4d (15-fluorobenzylidene-14-deoxy-11,12-didehydro-andrographolide) and A4e (15-bromoacylbenzylidene-14-deoxy-11,12-didehydro-andrographolide).

Abstract

A new depsidone, cowadepsidone (7), along with six known xanthones (1-6) were isolated from the twigs of Garcinia cowa. Their structures were determined on the basis of spectroscopic methods. The cytotoxicity against KB, MCF-7 and NCI-H187 cancer cell lines of compounds 2-7 were also reported.

*Department of Bioengineering, Bourns College of Engineering, University of California at Riverside, 900 University Avenue, Riverside, CA 92521, U.S.A.

Abstract

GW1100 is an antagonist of GPR40 identified by high throughput screening recently. The feasible synthesis of GW1100 has been developed in mild conditions. The key step involves the cyclization of the 2-thiouracil heterocycle under acidic conditions at room temperature.